WO2006058731A2 - Strahlungshärtbare beschichtungsmassen - Google Patents
Strahlungshärtbare beschichtungsmassen Download PDFInfo
- Publication number
- WO2006058731A2 WO2006058731A2 PCT/EP2005/012795 EP2005012795W WO2006058731A2 WO 2006058731 A2 WO2006058731 A2 WO 2006058731A2 EP 2005012795 W EP2005012795 W EP 2005012795W WO 2006058731 A2 WO2006058731 A2 WO 2006058731A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- alkyl
- optionally substituted
- aryl
- coating compositions
- Prior art date
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- 238000000576 coating method Methods 0.000 title claims abstract description 27
- 239000011248 coating agent Substances 0.000 title claims abstract description 20
- 239000000126 substance Substances 0.000 title abstract description 5
- 239000000203 mixture Substances 0.000 claims abstract description 49
- -1 cyanine cation Chemical class 0.000 claims description 251
- 150000001450 anions Chemical class 0.000 claims description 42
- 239000008199 coating composition Substances 0.000 claims description 42
- 150000003254 radicals Chemical class 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 26
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 18
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 18
- 239000003999 initiator Substances 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 239000003973 paint Substances 0.000 claims description 17
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 125000003107 substituted aryl group Chemical group 0.000 claims description 16
- 239000001301 oxygen Substances 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 13
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 12
- 230000005855 radiation Effects 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 8
- 239000011230 binding agent Substances 0.000 claims description 8
- 239000003085 diluting agent Substances 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 150000002978 peroxides Chemical class 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical class [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 claims description 7
- 150000003457 sulfones Chemical class 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000004104 aryloxy group Chemical group 0.000 claims description 5
- 150000001768 cations Chemical class 0.000 claims description 5
- 239000003086 colorant Substances 0.000 claims description 5
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 5
- 239000011261 inert gas Substances 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 239000012298 atmosphere Substances 0.000 claims description 3
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 claims description 3
- 239000004566 building material Substances 0.000 claims description 3
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 3
- URSLCTBXQMKCFE-UHFFFAOYSA-N dihydrogenborate Chemical compound OB(O)[O-] URSLCTBXQMKCFE-UHFFFAOYSA-N 0.000 claims description 3
- 239000004922 lacquer Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 3
- 125000002723 alicyclic group Chemical group 0.000 claims description 2
- 239000002969 artificial stone Substances 0.000 claims description 2
- 125000005324 aryloxy alkyloxy group Chemical group 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 239000011449 brick Substances 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical class OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims 1
- 238000009472 formulation Methods 0.000 abstract description 6
- 239000000049 pigment Substances 0.000 description 28
- 239000000975 dye Substances 0.000 description 26
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical class [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 11
- 238000010521 absorption reaction Methods 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 8
- 239000000945 filler Substances 0.000 description 8
- 230000001235 sensitizing effect Effects 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000006096 absorbing agent Substances 0.000 description 7
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000012965 benzophenone Substances 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 244000028419 Styrax benzoin Species 0.000 description 5
- 235000000126 Styrax benzoin Nutrition 0.000 description 5
- 235000008411 Sumatra benzointree Nutrition 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 235000019382 gum benzoic Nutrition 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 4
- ISAOCJYIOMOJEB-UHFFFAOYSA-N desyl alcohol Natural products C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 4
- 239000010408 film Substances 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 238000007639 printing Methods 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 4
- 239000004408 titanium dioxide Substances 0.000 description 4
- LWNGJAHMBMVCJR-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenoxy)boronic acid Chemical compound OB(O)OC1=C(F)C(F)=C(F)C(F)=C1F LWNGJAHMBMVCJR-UHFFFAOYSA-N 0.000 description 3
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 3
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 3
- NJWGQARXZDRHCD-UHFFFAOYSA-N 2-methylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3C(=O)C2=C1 NJWGQARXZDRHCD-UHFFFAOYSA-N 0.000 description 3
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 3
- 229910017008 AsF 6 Inorganic materials 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229910018286 SbF 6 Inorganic materials 0.000 description 3
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 3
- LFOXEOLGJPJZAA-UHFFFAOYSA-N [(2,6-dimethoxybenzoyl)-(2,4,4-trimethylpentyl)phosphoryl]-(2,6-dimethoxyphenyl)methanone Chemical compound COC1=CC=CC(OC)=C1C(=O)P(=O)(CC(C)CC(C)(C)C)C(=O)C1=C(OC)C=CC=C1OC LFOXEOLGJPJZAA-UHFFFAOYSA-N 0.000 description 3
- 150000004056 anthraquinones Chemical class 0.000 description 3
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 3
- 229940077388 benzenesulfonate Drugs 0.000 description 3
- 229960002130 benzoin Drugs 0.000 description 3
- 150000008366 benzophenones Chemical class 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000001723 curing Methods 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 3
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000010445 mica Substances 0.000 description 3
- 229910052618 mica group Inorganic materials 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 3
- HPAFOABSQZMTHE-UHFFFAOYSA-N phenyl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)C1=CC=CC=C1 HPAFOABSQZMTHE-UHFFFAOYSA-N 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000010526 radical polymerization reaction Methods 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- CHYBTAZWINMGHA-UHFFFAOYSA-N tetraoctylazanium Chemical compound CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC CHYBTAZWINMGHA-UHFFFAOYSA-N 0.000 description 3
- 239000002562 thickening agent Substances 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- WXPWZZHELZEVPO-UHFFFAOYSA-N (4-methylphenyl)-phenylmethanone Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=CC=C1 WXPWZZHELZEVPO-UHFFFAOYSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- VUIMBZIZZFSQEE-UHFFFAOYSA-N 1-(1h-indol-3-yl)ethanone Chemical compound C1=CC=C2C(C(=O)C)=CNC2=C1 VUIMBZIZZFSQEE-UHFFFAOYSA-N 0.000 description 2
- LDMOEFOXLIZJOW-UHFFFAOYSA-N 1-dodecanesulfonic acid Chemical compound CCCCCCCCCCCCS(O)(=O)=O LDMOEFOXLIZJOW-UHFFFAOYSA-N 0.000 description 2
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 2
- XHLHPRDBBAGVEG-UHFFFAOYSA-N 1-tetralone Chemical compound C1=CC=C2C(=O)CCCC2=C1 XHLHPRDBBAGVEG-UHFFFAOYSA-N 0.000 description 2
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidine Chemical compound CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 2
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 2
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 2
- YIHXNPFYGVDVAX-UHFFFAOYSA-N 2,4-bis(3-chlorophenyl)-6-(trichloromethyl)-1,3,5-triazine Chemical compound ClC1=CC=CC(C=2N=C(N=C(N=2)C=2C=C(Cl)C=CC=2)C(Cl)(Cl)Cl)=C1 YIHXNPFYGVDVAX-UHFFFAOYSA-N 0.000 description 2
- QTUVQQKHBMGYEH-UHFFFAOYSA-N 2-(trichloromethyl)-1,3,5-triazine Chemical compound ClC(Cl)(Cl)C1=NC=NC=N1 QTUVQQKHBMGYEH-UHFFFAOYSA-N 0.000 description 2
- JWKRKQYJIZLNFB-UHFFFAOYSA-N 2-[2-(4-chlorophenyl)ethenyl]-4,6-bis(trichloromethyl)-1,3,5-triazine Chemical compound C1=CC(Cl)=CC=C1C=CC1=NC(C(Cl)(Cl)Cl)=NC(C(Cl)(Cl)Cl)=N1 JWKRKQYJIZLNFB-UHFFFAOYSA-N 0.000 description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
- LKAWUMIKIKUXHV-UHFFFAOYSA-N 4-[4,6-bis(trichloromethyl)-1,3,5-triazin-2-yl]aniline Chemical compound C1=CC(N)=CC=C1C1=NC(C(Cl)(Cl)Cl)=NC(C(Cl)(Cl)Cl)=N1 LKAWUMIKIKUXHV-UHFFFAOYSA-N 0.000 description 2
- NTPLXRHDUXRPNE-UHFFFAOYSA-N 4-methoxyacetophenone Chemical compound COC1=CC=C(C(C)=O)C=C1 NTPLXRHDUXRPNE-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical compound CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
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- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 238000011417 postcuring Methods 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000002987 primer (paints) Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- NQLVQOSNDJXLKG-UHFFFAOYSA-N prosulfocarb Chemical compound CCCN(CCC)C(=O)SCC1=CC=CC=C1 NQLVQOSNDJXLKG-UHFFFAOYSA-N 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- RQGPLDBZHMVWCH-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole Chemical compound C1=NC2=CC=NC2=C1 RQGPLDBZHMVWCH-UHFFFAOYSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 150000008584 quinuclidines Chemical class 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000979 synthetic dye Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- 125000005490 tosylate group Chemical group 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 239000001003 triarylmethane dye Substances 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- DWWMSEANWMWMCB-UHFFFAOYSA-N tribromomethylsulfonylbenzene Chemical compound BrC(Br)(Br)S(=O)(=O)C1=CC=CC=C1 DWWMSEANWMWMCB-UHFFFAOYSA-N 0.000 description 1
- GFVKHYGXCQWRON-UHFFFAOYSA-N tributyl(ethyl)azanium Chemical compound CCCC[N+](CC)(CCCC)CCCC GFVKHYGXCQWRON-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- VZUBRRXYUOJBRS-UHFFFAOYSA-N trichloromethylsulfonylbenzene Chemical compound ClC(Cl)(Cl)S(=O)(=O)C1=CC=CC=C1 VZUBRRXYUOJBRS-UHFFFAOYSA-N 0.000 description 1
- SEACXNRNJAXIBM-UHFFFAOYSA-N triethyl(methyl)azanium Chemical compound CC[N+](C)(CC)CC SEACXNRNJAXIBM-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical compound C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 1
- 239000012953 triphenylsulfonium Substances 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- 238000001132 ultrasonic dispersion Methods 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- XKGLSKVNOSHTAD-UHFFFAOYSA-N valerophenone Chemical compound CCCCC(=O)C1=CC=CC=C1 XKGLSKVNOSHTAD-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 150000007964 xanthones Chemical class 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/029—Inorganic compounds; Onium compounds; Organic compounds having hetero atoms other than oxygen, nitrogen or sulfur
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/031—Organic compounds not covered by group G03F7/029
Definitions
- EP 408 322 describes one-component photoinitiators in the form of the salts of cyanine dye and certain borane ions.
- This invention describes two-component NIR photoinitiator systems which contain at least one sensitizer dye, also called sensitizer, and at least one free radical initiator, also called co-initiator.
- compositions are known, which are prepared from the separate salts of a cationic dye and boranate salts and can also be used in mixtures with UV photoinitiators.
- the object of the present invention was to provide NIR photoinitiator systems which on the one hand have good solubility and on the other hand have good photoactivability by NIR radiation.
- n 1 or 2 and the radicals R to R are the following:
- Preferred anions AnA " are BF 4 ' , PF 6 ' , AsF 6 ' , SbF 6 " , CIO 4 “ , Cl “ , Br “ , tetraphenylborate, tetrakis (pentafluorophenyl) borate, the benzenesulfonate anion, the p-toluenesulfonate anion and the trifluoromethanesulfonate anion.
- Preferred anions AnC are BF 4 " , PF 6 “ , AsF 6 “ , SbF 6 “ , CIO 4 “ , Cl “ , Br “ , tetraphenylborate, tetrakis (pentafluorophenyl) borate, the benzenesulfonate anion, the p-toluenesulfonate anion and the trifluoromethanesulfonate anion.
- Reactive diluents (E) are, for example, esters of (meth) acrylic acid with alcohols having from 1 to 20 carbon atoms, e.g. Methyl (meth) acrylate, (meth) acrylic acid ethyl ester, butyl (meth) acrylate, (meth) acrylic acid 2-ethylhexyl ester, 2-hydroxyethyl acrylate, 4-hydroxybutyl acrylate, dihydrodicyclopentadienyl acrylate, vinyl aromatic compounds, e.g. Styrene, divinylbenzene, ⁇ , ⁇ -unsaturated nitriles, e.g.
- esters of (meth) acrylic acid with alcohols having from 1 to 20 carbon atoms e.g. Methyl (meth) acrylate, (meth) acrylic acid ethyl ester, butyl (meth) acrylate, (meth) acrylic acid 2-ethylhex
- UV photoinitiators As UV photoinitiators (F), photoinitiators known to those skilled in the art can be used, e.g. those in "Advances in Polymer Science", Volume 14, Springer Berlin 1974 or in K.K. Dietliker, Chemistry and Technology of UV and EB Formulation for Coatings, Inks and Paints, Volume 3; Photoinitiators for Free Radical and Cationic Polymerization, P.K.T. Oldring (Eds), SITA Technology Ltd, London.
- Phosphine oxides are, for example, mono- or bisacylphosphine oxides, as described, for example, in US Pat. EP-A 7 508, EP-A 57 474, DE-A 196 18 720, EP-A 495 751 or EP-A 615 980, for example 2,4,6-trimethylbenzoyldiphenylphosphine oxide, ethyl 2,4,6 trimethylbenzoylphenylphosphinate or bis (2,6-dimethoxybenzoyl) -2,4,4-trimethylpentylphosphine oxide,
- At least one UV photoinitiator is present in the coating compositions according to the invention.
- practically insoluble means a solubility at 25 ° C. of less than 1 g / 1000 g of application medium, preferably less than 0.5, more preferably less than 0.25, very preferably less than 0.1 and in particular less than 0.05 g / 1000 g of application medium.
- the coloring absorption pigments are, for example, customary organic or inorganic absorption pigments which can be used in the coatings industry.
- organic absorption pigments are azo pigments, phthalocyanine, quinacridone and pyrrolopyrrole pigments.
- inorganic absorption pigments are iron oxide pigments, titanium dioxide and carbon black.
- Dyes are also colorants and differ from the pigments by their solubility in the application medium, ie they have at 25 0 C, a solubility above 1 g / 1000 g in the application medium.
- dyes examples include azo, azine, anthraquinone, acridine, cyanine, oxazine, polymethine, thiazine, triarylmethane dyes. These dyes may find application as basic or cationic dyes, mordant, direct, disperse, development, vat, metal complex, reactive, acid, sulfur, coupling or substantive dyes.
- one or more photochemically and / or thermally activatable initiators can be added, for example potassium peroxodisulfate, dibenzoyl peroxide, cyclohexanone peroxide, di-tert-butyl peroxide, azobis / so-butyronitrile, cyclohexylsulfonyl acetyl peroxide, di- / so-propyl percarbonate, fin Butyl peroctoate or benzpinacol, as well as, for example, example, such thermally activatable initiators having a half life at 80 0 C of more than 100 hours, such as di-t-butyl peroxide, cumene hydroperoxide, dicumyl peroxide, t-butyl perbenzoate, silylated pinacols, z.
- potassium peroxodisulfate for example potassium peroxodisulfate, dibenzoyl peroxide, cyclohexanone peroxid
- the blends of the present invention are useful as NIR-activatable photoinitiators and exhibit better solubility in coating compositions and coating systems than the prior art formulations of NIR photoinitiators which utilize borate ions of formula (VII) as counterion to the cyanine cation act.
- This has the consequence that on the one hand the photoinitiator can be distributed more uniformly in the paint system and in the later paint no undissolved particles remain as defects and on the other hand results in a higher photoreactivity.
- the compounds precipitate in part because of the lack of solubility as crystals in the coating composition.
- mixing takes place.
- a mechanical stirrer for example disc, angled blade, anchor, intensive or gassing, but also by pumping, optionally by a slit, or in a mixing pump, or often by a simple mixture of the two components by hand or by shaking.
- mixing techniques with higher shear energy such as. Beam dispersion, intensive, Ultraturrax- or ultrasonic dispersion, can be used.
- coating compositions which have a layer thickness of more than 30 microns, preferably more than 45 and more preferably more than 60 microns.
- the coating compositions may have a thickness of up to 300, preferably up to 250 and more preferably up to 200 microns.
- the coatings can also be applied thicker or thinner, for example from 10 to 1000 microns. However, it may be necessary to irradiate several times with very thick applied coating compositions.
- the radiation-curable coating composition may preferably be prepared in a simple manner, e.g. by spraying, filling, brushing, knife-coating, brushing, rolling, rolling, pouring, dewaxing, laminating, back-molding or co-extruding, etc., onto the object to be coated and dried if necessary.
- the irradiation can also be carried out in the absence of oxygen.
- the irradiation is carried out so that the coating composition is exposed to an oxygen partial pressure of less than 18 kPa at the moment of its irradiation with NIR radiation.
- the relevant areas are the surface areas of the object to be coated provided with the radiation-curable coating compositions at the moment of exposure.
- the oxygen partial pressure is not more than 17 kPa, more preferably not more than 15.3 kPa, most preferably not more than 13.5 kPa, especially not more than 10 kPa and especially not more than 6.3 kPa.
- oxygen partial pressure preferably does not need to fall below 0.5 kPa, more preferably 0.9 kPa, most preferably 1, 8 kPa and especially 2.5 kPa.
- Such a low oxygen partial pressure can advantageously be achieved by diluting the oxygen-containing atmosphere with at least one inert gas or replacing it with at least one inert gas, ie gases which are unreactive under the radiation curing conditions.
- inert gases are preferably nitrogen, noble gases, carbon dioxide or combustion gases.
- the proportion of the at least one inert gas should be more than 80% by volume, preferably at least 85, more preferably at least 90, most preferably at least 95 and in particular at least 98% by volume.
- the irradiation can be carried out by covering the coating mass with transparent media.
- Transparent media are z.
- plastic films glass or liquids, eg water.
- the irradiation is particularly preferably carried out as described in WO 01/14483, to which reference is hereby made in its entirety. Very particular preference is given to irradiation in the manner described in DE-A1 199 57 900, to which reference is hereby made in its entirety.
- the coating compositions according to the invention are particularly preferably suitable for exterior coatings or in applications which are exposed to daylight, preferably of buildings or building parts, interior coatings, coatings on vehicles and aircraft.
- the coating compositions according to the invention are used as or in automotive clearcoats and topcoats and in paints, in particular facade paints, industrial coatings, coil coatings, moldings, castings or dental compositions.
- the coating compositions according to the invention are advantageously to be used for decorative painting, in particular for furniture, parquet, laminate and floor coverings.
- the synthesized NIR sensitizers A1 to A10 according to the invention are summarized in Table 1.
- the non-inventive NIR dyes in the form of the corresponding iodides (B1 to B10) are used as comparative examples.
- the customary anion is exchanged for an anion according to the invention.
- NIR sensitizers of the invention having improved solubilities have been synthesized.
- the compound was prepared as follows: 0.003 mol (1.6 g) of the NIR sensitizer A1 were initially charged together with 0.009 mol (2.3 g) of Na dodecylsulfonate in 50 ml of dichloromethane. 50 ml of water were added, stirred for 30 minutes at room temperature and finally the phases were separated. The organic phase was washed three times with 50 ml of water until no iodide was detectable in the wash water with silver nitrate solution. After drying the organic phase with sodium sulfate, the solvent was distilled off and the residue was dried at 50 ° C. in vacuo.
- the non-inventive NIR sensitizers B7, B11 and B12 were insufficiently soluble in both solutions (solubility in each case ⁇ 0.1% by weight).
- the non-inventive NIR sensitizers B7, B11, B12 were not completely dissolved in the coating raw material. After exposure, an incompletely cured paint film was obtained. In addition, there were colored specks in the paint (undissolved crystals under the polarizing microscope).
Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP05850218A EP1820064A2 (de) | 2004-12-03 | 2005-12-01 | Strahlungshärtbare beschichtungsmassen |
JP2007543769A JP4896886B2 (ja) | 2004-12-03 | 2005-12-01 | 放射線硬化可能な被覆組成物 |
CN2005800415850A CN101069129B (zh) | 2004-12-03 | 2005-12-01 | 可辐射固化的涂料 |
US11/720,788 US20100126386A1 (en) | 2004-12-03 | 2005-12-01 | Radiation-curable coating substances |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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DE102004058584.9 | 2004-12-03 | ||
DE102004058584A DE102004058584A1 (de) | 2004-12-03 | 2004-12-03 | Strahlungshärtbare Beschichtungsmassen |
Publications (2)
Publication Number | Publication Date |
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WO2006058731A2 true WO2006058731A2 (de) | 2006-06-08 |
WO2006058731A3 WO2006058731A3 (de) | 2006-10-05 |
Family
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PCT/EP2005/012795 WO2006058731A2 (de) | 2004-12-03 | 2005-12-01 | Strahlungshärtbare beschichtungsmassen |
Country Status (6)
Country | Link |
---|---|
US (1) | US20100126386A1 (de) |
EP (1) | EP1820064A2 (de) |
JP (2) | JP4896886B2 (de) |
CN (1) | CN101069129B (de) |
DE (1) | DE102004058584A1 (de) |
WO (1) | WO2006058731A2 (de) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2008058885A2 (de) * | 2006-11-17 | 2008-05-22 | Basf Se | Strahlungshärtbare beschichtungsmassen |
EP1995285A1 (de) * | 2007-05-21 | 2008-11-26 | Hexion Specialty Chemicals Research Belgium S.A. | Lichthärtbare Zusammensetzungen für Farbe zur Straßenkennzeichnung |
US8129455B2 (en) | 2007-07-10 | 2012-03-06 | Styrolution GmbH | Flame retardant thermoplastic molding compositions |
US8575269B2 (en) | 2007-09-14 | 2013-11-05 | Styrolution GmbH | Transparent, tough and rigid molding compositions based on styrene-butadiene block copolymer mixtures |
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EP2098367A1 (de) * | 2008-03-05 | 2009-09-09 | Eastman Kodak Company | Sensibilisator/Initiator-Kombination für negativ arbeitende wärmeempfindliche Zusammensetzungen für Lithografieplatten |
EP2356182B1 (de) * | 2008-11-12 | 2015-05-06 | Basf Se | Strahlungshärtbare beschichtungsmassen |
KR20100099048A (ko) * | 2009-03-02 | 2010-09-10 | 주식회사 동진쎄미켐 | 감광성 수지 조성물 |
US8729307B2 (en) * | 2009-10-26 | 2014-05-20 | National Institute Of Advanced Industrial Science And Technology | Photoresponsive ionic organic compound, method of producing the same, and photoresponsive carbon nanotube dispersant comprising said ionic organic compound |
EP2450893A1 (de) * | 2010-11-08 | 2012-05-09 | Bayer MaterialScience AG | Photopolymer-Formulierung zur Herstellung holographischer Medien mit hoch vernetzten Matrixpolymeren |
EP3314607A1 (de) * | 2015-06-23 | 2018-05-02 | Covestro Deutschland AG | Holographische medien enthaltend ketten-substituierte cyaninfarbstoffe |
CN107300830B (zh) * | 2016-04-15 | 2021-03-30 | 常州强力电子新材料股份有限公司 | 一种新型光固化组合物及其应用 |
WO2019039136A1 (ja) * | 2017-08-21 | 2019-02-28 | 富士フイルム株式会社 | 着色組成物、硬化膜、パターン形成方法、カラーフィルタ、固体撮像素子および画像表示装置 |
EP3501837A1 (de) * | 2017-12-21 | 2019-06-26 | Université de Haute Alsace | Thermische verstärkung der durch rot- bis nahinfrarot-bestrahlung induzierten radikalischen polymerisation |
EP3981841A1 (de) * | 2020-10-06 | 2022-04-13 | Sika Technology Ag | Bodenbelag enthaltend uv-nachweisbare grundierung |
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EP1314725B1 (de) * | 2000-08-30 | 2008-03-19 | Wako Pure Chemical Industries, Ltd. | Sulphoniumsalz-verbindung |
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JP2002122988A (ja) * | 2000-10-13 | 2002-04-26 | Mitsubishi Chemicals Corp | 光重合性組成物及び光重合性平版印刷版 |
JP2003113329A (ja) * | 2002-07-25 | 2003-04-18 | Sony Corp | 疎水化カチオン染料及びこれを用いた熱転写インクリボン |
-
2004
- 2004-12-03 DE DE102004058584A patent/DE102004058584A1/de not_active Withdrawn
-
2005
- 2005-12-01 JP JP2007543769A patent/JP4896886B2/ja not_active Expired - Fee Related
- 2005-12-01 US US11/720,788 patent/US20100126386A1/en not_active Abandoned
- 2005-12-01 EP EP05850218A patent/EP1820064A2/de not_active Withdrawn
- 2005-12-01 CN CN2005800415850A patent/CN101069129B/zh not_active Expired - Fee Related
- 2005-12-01 WO PCT/EP2005/012795 patent/WO2006058731A2/de active Application Filing
-
2011
- 2011-04-18 JP JP2011092059A patent/JP2011149029A/ja active Pending
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EP0223587A1 (de) | 1985-11-20 | 1987-05-27 | The Mead Corporation | Ionische Farbstoffe als Initiatoren enthaltende fotosensitive Materialien |
EP0408322A1 (de) | 1989-07-10 | 1991-01-16 | The Mead Corporation | Farbstoffboratkomplexe |
EP1359008A1 (de) | 2002-04-29 | 2003-11-05 | Agfa-Gevaert | Strahlungsempfindliches Gemisch und damit hergestelltes Aufzeichnungsmaterial |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2008058885A2 (de) * | 2006-11-17 | 2008-05-22 | Basf Se | Strahlungshärtbare beschichtungsmassen |
WO2008058885A3 (de) * | 2006-11-17 | 2008-07-31 | Basf Se | Strahlungshärtbare beschichtungsmassen |
EP1995285A1 (de) * | 2007-05-21 | 2008-11-26 | Hexion Specialty Chemicals Research Belgium S.A. | Lichthärtbare Zusammensetzungen für Farbe zur Straßenkennzeichnung |
WO2008141743A1 (en) * | 2007-05-21 | 2008-11-27 | Hexion Specialty Chemicals Research Belgium S.A. | Photocurable compositions for road marking paint |
US8129455B2 (en) | 2007-07-10 | 2012-03-06 | Styrolution GmbH | Flame retardant thermoplastic molding compositions |
US8575269B2 (en) | 2007-09-14 | 2013-11-05 | Styrolution GmbH | Transparent, tough and rigid molding compositions based on styrene-butadiene block copolymer mixtures |
Also Published As
Publication number | Publication date |
---|---|
CN101069129A (zh) | 2007-11-07 |
JP2011149029A (ja) | 2011-08-04 |
JP2008521982A (ja) | 2008-06-26 |
DE102004058584A1 (de) | 2006-06-08 |
WO2006058731A3 (de) | 2006-10-05 |
EP1820064A2 (de) | 2007-08-22 |
JP4896886B2 (ja) | 2012-03-14 |
US20100126386A1 (en) | 2010-05-27 |
CN101069129B (zh) | 2010-12-08 |
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